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Depends on his taste and your style.
I’d go with a skirt or a short dress, but it’s hard to give advice without seeing what those clothes look like. Appearance of each piece of clothes probably has more influence than the exact type of dress. Can you find an example from the internet showing approximately what clothes you have look like?
In my view somewhat shorter dresses go along lot more with the idea of a sexy dinner than long dresses. However, if a different dress makes you look sexier in some other way, go with that one.
Can i See some?
It’s hard to say anything without seeing this, but I would have preferred a flirty image. something like a short skirt, not tight, but also a tight t-shirt
I’d wear a short fitted blazer dress with thigh high stockings, Lacey garters and high heels🙌🏼.
If he has a favorite sports team you wear a jersey and tell him he can have it (back) if he takes it , wink wink
Little black dress that looks dressy and classy. Subtle jewellery.
Underneath – quarter cup bra and open crotch panties.
I would definitely go with a tight black (sleep) dress that goes just at the start of your thigh. probably lace just above your clevage line and at the bottom lining of the dress, i found that goes pretty well with any long (thigh high) socks.
oh, i just checked that sweater dress link, definitely go with that.